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ALD00606

Sigma-Aldrich

Wang−Yu non-directed C−H functionalization ligand

95%

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About This Item

Empirical Formula (Hill Notation):
C7H3F6NO
CAS Number:
38609-76-6
Molecular Weight:
231.10
MDL number:
MFCD28802532
UNSPSC Code:
12352200
NACRES:
NA.22

Assay

95%

form

powder or crystals

reaction suitability

reaction type: C-C Bond Formation
reagent type: catalyst
reaction type: C-H Activation

mp

145 °C

storage temp.

−20°C

Related Categories

Application

This 2-pyridone ligand developed in the laboratory of Jin-Quan Yu binds to palladium and accelerates non-directed C-H functionalization. Developed for C-H olefination and carboxylation with arene as the limiting reagent, the Wang-Yu ligand enables diversification of drugs, synthetic intermediates, and other bioactive small molecules.

Other Notes

Ligand-accelerated non-directed C-H functionalization of arenes

Ligand-Promoted meta-C-H Functionalization of Benzylamines

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCH6157

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Peng Wang et al.
Angewandte Chemie (International ed. in English), 56(18), 5125-5129 (2017-04-04)
Meta-C-H functionalization of benzylamines has been developed using a PdII /transient mediator strategy. Using 2-pyridone ligands and 2-carbomethoxynorbornene (NBE-CO2 Me) as the mediator, arylation, amination, and chlorination of benzylamines are realized. This protocol features a broad substrate scope and is
Peng Wang et al.
Nature, 551(7681), 489-493 (2017-11-24)
The directed activation of carbon-hydrogen bonds (C-H) is important in the development of synthetically useful reactions, owing to the proximity-induced reactivity and selectivity that is enabled by coordinating functional groups. Palladium-catalysed non-directed C-H activation could potentially enable further useful reactions
Direct perfluoroalkylation including trifluoromethylation of aromatics with perfluoro carboxylic acids mediated by xenon difluoride.
Tanabe Y, et al.
The Journal of Organic Chemistry, 53 (19), 4582?4585-4582?4585 (1988)
Jin Lin et al.
Nature communications, 8, 14353-14353 (2017-02-07)
Catalytic oxidative C-H bond functionalization reactions that proceed without requiring stoichiometric amounts of external oxidants or pre-functionalized oxidizing reagents could maximize the atom- and step-economy in chemical syntheses. However, such a transformation remains elusive. Here, we report that a photo-driven

Related Content

Yu Group – Professor Product Portal

The Yu program centers around the discovery of catalytic carbon–carbon and carbon–heteroatom bond forming reactions based on C–H activation. Target transformations are selected to enable 1) the use of simple and abundant starting materials such as aliphatic acids, amines and alcohols, and 2) disconnections that drastically shorten the synthesis of a drug molecule or a major class of biologically active compounds.

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